Oxidative C(sp3)-C(sp3) bond cleavage reaction of an isopropyl group to give an acetyl group upon O2-treatment of a labile cationic ruthenium species, [Tp(iPr)Ru(dppene)(OH2)]+

Chemical Communications

Volumn , Issue 16, 1999, Pages 1491-1492

  Takahashi, Yoshiaki ^a   Hikichi, Shiro ^a   Akita, Munetaka ^a   Moro Oka, Yoshihiko ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; LIGAND; OXYGEN; RUTHENIUM;

ARTICLE; ENVIRONMENTAL TEMPERATURE; OXIDATION;

EID: 0033592175     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a904218k     Document Type: Article

References (24)

1. Leading references: R. A. Sheldon and J. K. Kochi, Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, New York, 1981; The Chemistry of Peroxides, ed. S. Patai, John Wiley & Sons, Chichester, 1983; Oxygen Complexes and Oxygen Activation by Transition Metals, ed. A. E. Martel and D. T. Sawyer, Plenum Press, New York, 1988; Organic Peroxides, ed. W. Ando, John Wiley and Sons, Chichester, 1992; Thematic issue of Chem. Rev. (Metal-Dioxygen Complexes), Chem. Rev., 1994, 94, 567; G. Strukul, Angew. Chem., Int. Ed. Engl., 1998, 37, 1198; S. Murahashi, Angew. Chem., Int. Ed. Engl., 1995, 34, 2443.
2. Leading references: R. A. Sheldon and J. K. Kochi, Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, New York, 1981; The Chemistry of Peroxides, ed. S. Patai, John Wiley & Sons, Chichester, 1983; Oxygen Complexes and Oxygen Activation by Transition Metals, ed. A. E. Martel and D. T. Sawyer, Plenum Press, New York, 1988; Organic Peroxides, ed. W. Ando, John Wiley and Sons, Chichester, 1992; Thematic issue of Chem. Rev. (Metal-Dioxygen Complexes), Chem. Rev., 1994, 94, 567; G. Strukul, Angew. Chem., Int. Ed. Engl., 1998, 37, 1198; S. Murahashi, Angew. Chem., Int. Ed. Engl., 1995, 34, 2443.
3. Leading references: R. A. Sheldon and J. K. Kochi, Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, New York, 1981; The Chemistry of Peroxides, ed. S. Patai, John Wiley & Sons, Chichester, 1983; Oxygen Complexes and Oxygen Activation by Transition Metals, ed. A. E. Martel and D. T. Sawyer, Plenum Press, New York, 1988; Organic Peroxides, ed. W. Ando, John Wiley and Sons, Chichester, 1992; Thematic issue of Chem. Rev. (Metal-Dioxygen Complexes), Chem. Rev., 1994, 94, 567; G. Strukul, Angew. Chem., Int. Ed. Engl., 1998, 37, 1198; S. Murahashi, Angew. Chem., Int. Ed. Engl., 1995, 34, 2443.
4. Leading references: R. A. Sheldon and J. K. Kochi, Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, New York, 1981; The Chemistry of Peroxides, ed. S. Patai, John Wiley & Sons, Chichester, 1983; Oxygen Complexes and Oxygen Activation by Transition Metals, ed. A. E. Martel and D. T. Sawyer, Plenum Press, New York, 1988; Organic Peroxides, ed. W. Ando, John Wiley and Sons, Chichester, 1992; Thematic issue of Chem. Rev. (Metal-Dioxygen Complexes), Chem. Rev., 1994, 94, 567; G. Strukul, Angew. Chem., Int. Ed. Engl., 1998, 37, 1198; S. Murahashi, Angew. Chem., Int. Ed. Engl., 1995, 34, 2443.
5. Leading references: R. A. Sheldon and J. K. Kochi, Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, New York, 1981; The Chemistry of Peroxides, ed. S. Patai, John Wiley & Sons, Chichester, 1983; Oxygen Complexes and Oxygen Activation by Transition Metals, ed. A. E. Martel and D. T. Sawyer, Plenum Press, New York, 1988; Organic Peroxides, ed. W. Ando, John Wiley and Sons, Chichester, 1992; Thematic issue of Chem. Rev. (Metal-Dioxygen Complexes), Chem. Rev., 1994, 94, 567; G. Strukul, Angew. Chem., Int. Ed. Engl., 1998, 37, 1198; S. Murahashi, Angew. Chem., Int. Ed. Engl., 1995, 34, 2443.
6. Leading references: R. A. Sheldon and J. K. Kochi, Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, New York, 1981; The Chemistry of Peroxides, ed. S. Patai, John Wiley & Sons, Chichester, 1983; Oxygen Complexes and Oxygen Activation by Transition Metals, ed. A. E. Martel and D. T. Sawyer, Plenum Press, New York, 1988; Organic Peroxides, ed. W. Ando, John Wiley and Sons, Chichester, 1992; Thematic issue of Chem. Rev. (Metal-Dioxygen Complexes), Chem. Rev., 1994, 94, 567; G. Strukul, Angew. Chem., Int. Ed. Engl., 1998, 37, 1198; S. Murahashi, Angew. Chem., Int. Ed. Engl., 1995, 34, 2443.
7. Leading references: R. A. Sheldon and J. K. Kochi, Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, New York, 1981; The Chemistry of Peroxides, ed. S. Patai, John Wiley & Sons, Chichester, 1983; Oxygen Complexes and Oxygen Activation by Transition Metals, ed. A. E. Martel and D. T. Sawyer, Plenum Press, New York, 1988; Organic Peroxides, ed. W. Ando, John Wiley and Sons, Chichester, 1992; Thematic issue of Chem. Rev. (Metal-Dioxygen Complexes), Chem. Rev., 1994, 94, 567; G. Strukul, Angew. Chem., Int. Ed. Engl., 1998, 37, 1198; S. Murahashi, Angew. Chem., Int. Ed. Engl., 1995, 34, 2443.
8. See ref. 4(b) and references cited therein. For C=C cleavage reactions, see, for example, our paper dealing with model complexes of catechol dioxygenase. T. Ogihara, S. Hikichi, M. Akita and Y. Moro-oka, Inorg. Chem., 1998, 37, 2614.
9. Metalloenzymes which catalyze fragmentation of carbon skeleton via C-C cleavage (e.g. P-450) are known. V. Stajek, M. Miksch, P. Lueer, U. Matern and W. Boland, Angew. Chem., Int. Ed ., 1999, 38, 400.
10. 2: (a) M. Akita, T. Miyaji, S. Hikichi and Y. Moro-oka, Chem. Commun., 1998, 1005; Co-OOR:
11. (b) S. Hikichi, H. Komatsuzaki, M. Akita and Y. Moro-oka, J. Am. Chem. Soc., 1998, 120, 4699; Co, Nioxo;
12. 2:
13. (d) H. Komatsuzaki, Y. Nagasu, K. Suzuki, T. Shibasaki, M. Satoh, F. Ebina, S. Hikichi, M. Akita and Y. Moro-oka, J. Chem. Soc., Dalton Trans., 1998, 511;
14. 2:
15. (f) M. Kosugi, S. Hikichi, M. Akita and Y. Moro-oka, J. Chem. Soc., Dalton Trans., 1999, 1369.
16. + and 6 were prepared according to the preparative method for the dppe complexes: see, Y. Takahashi, S. Hikichi, M. Akita and Y. Moro-oka, Inorg. Chem., 1998, 37, 3186.
17. + stabilized by an agostic interaction with a methyl C-H bond in the isopropyl group could be isolated. Y. Takahashi, S. Hikichi, M. Akita and Y. Moro-oka, Organometallics, 1999, 18, 2571.
18. + species. K. Kirchner, K. Mauthner, K. Mereiter and R. Schmid, J. Chem. Soc., Chem. Commun., 1993, 892; I de los Rios, M. J. Tenorio, J. Padilla, M. P. Puerta and P. Valerga, J. Chem. Soc., Dalton Trans., 1996, 377; M. Sato and M. Asai, J. Organomet. Chem., 1996, 508, 121.
19. + species. K. Kirchner, K. Mauthner, K. Mereiter and R. Schmid, J. Chem. Soc., Chem. Commun., 1993, 892; I de los Rios, M. J. Tenorio, J. Padilla, M. P. Puerta and P. Valerga, J. Chem. Soc., Dalton Trans., 1996, 377; M. Sato and M. Asai, J. Organomet. Chem., 1996, 508, 121.
20. + species. K. Kirchner, K. Mauthner, K. Mereiter and R. Schmid, J. Chem. Soc., Chem. Commun., 1993, 892; I de los Rios, M. J. Tenorio, J. Padilla, M. P. Puerta and P. Valerga, J. Chem. Soc., Dalton Trans., 1996, 377; M. Sato and M. Asai, J. Organomet. Chem., 1996, 508, 121.
21. Y. Takahashi, S. Hikichi, M. Akita and Y. Moro-oka, unpublished work.
22. RRh complex, only one report appeared. N. G. Connelly, D. J. H. Emslie, B. Metz, A. G. Orpen and M. J. Quayle, Chem. Commun., 1996, 2289.
23. RRh complex, only one report appeared. N. G. Connelly, D. J. H. Emslie, B. Metz, A. G. Orpen and M. J. Quayle, Chem. Commun., 1996, 2289.
24. L values defined and determined by Lever, the order of electron-donating ability is estimated as follows: dppene (0.49) > dppm (0.43) > dppe (0.28). A. B. P. Lever, Inorg. Chem., 1990, 29, 1271.